Bootstrapping, Working Remotely and Career Choices

How I Connected the Dots

The more I learn, the more I connect the dots.

For a few months now, two podcasts have been keeping me company while on the road. They are This Week in Startups and Startup School Radio. Hearing numerous startup people talk on different subjects cemented two of my beliefs, which were previously informed by books and personal experience.

I will use three examples from podcast excerpts to dive into the details.


On the July 31 episode of This Week in Startups, the host and angel investor Jason Calacanis shared his thoughts on how to bootstrap a business. I agree with him 100% on this, here’s what he said when an entrepreneur asked about getting the initial $10k, $20k to keep his startup going:

Having a client or patron for your product is a great idea, especially when you’re doing a SaaS business or enterprise software. It’s great to, before you build a product, make mockups and then approach ten clients and say to them “if you become my client and pay for the product a year in advance, I’ll give you exclusive access, I’ll customize the product for you, etc.”
Getting people who believe in you to pay you in advance will be one way. You’ll get a lot of ‘no’s but all you need is a few ‘yes’es from those who want to underwrite it, who want to see the product exist in the world, to get it started.
If not, there’s a really easy fallback. It is this: you work for 20 or 30 hours a week as a consultant, being a developer, designer, or salesperson, etc. Then you put your other 30 hours a week into (I’m assuming you’re a hustler who works 60 hours a week) your startup. You put your other half time in your startup. Then you slowly and incrementally make it better.
A true entrepreneur is not going to stop working on their startup just because they run out of money. They are going to hack it together; they are going to do it part-time; they are going to keep learning.
Let’s face it, if you don’t have the skills to get 20 to 30 hours a week of high paying consulting work, then you should step back and ask yourself, “why am I doing a startup?” You should be in the skills enhancement period of your career. Early in your career, you need to practice at building stuff and becoming good at something. Then you do a startup.
If you can’t get 10, 20, 30 hours a week of work at $50, $75, or $100 an hour, then you’re doing it wrong. Go get that skill, become a highly coveted person, sell yourself for 20 or 30 hours a week and then put the money to work in your startup. (40:30)

The key take away here is that first and foremost, you have to do great work. In order to play in the startup game, you’d need to have highly coveted skills.

Working Remotely

On August 14 episode of This Week in Startups, Jason was asked about how to get a remote working gig and how to get into the startup scene from the outside. Here’s how he answered.

The best way to get a remote gig going is to build a bit of a prescence for yourself, which means being an expert in something and putting your product out into the world. If I was an iOS developer, I would say “I’m really good at chat — if you want Slack like functionalities in your app, then I’m your guy.” Then you, as the iOS developer can create a blog about what different chat software programs are out there, what works and what doesn’t, etc. Build an online presence for yourself by showcasing your expertise — link to your projects, Github, etc.

Again, the bottomline comes to this point: you need to be an expert at what you do. But there is a key point to how that can be achieved, as Jason continued:

Then you can get in touch with the CTO and technical people at startups you want to work for. But the theme here is being targeted. Don’t be a general iOS developer, be specialized in something. For example, “I’m very good at the watch, here are some proofs of concepts I put together. I made a gallery of interesting projects around the watch. By the way, I’m available for work.”
Or say you’re good at interactions, you may make an app that showcases interesting interactions you came up with. You send that as a TestFlight to ten different CTOs and CEOs and say “I’m an iOS developer; I have lots of creative ideas; I’m really good at building interactions … these are the interactions I love most in the world, Path had this, Slack had this, Uber had that … I made an app out of all these interactions, I would love to send you a TestFlight of that app. And btw, I’m available for contract work or I’m available to join a startup full-time.”
That’s the kind of go-getter-ness you need to see in a remote worker. A remote worker is not going to get caught up in the culture and enthusiasm of an office. Mature (they could still be young), but mature and experienced workers can work really well. But you have to show that you’re self-motivated and self-driven and you G.S.D. Get Sugar Done. If you can’t G.S.D. on your own, you have no business being a remote worker. You have to prove it to a certain extent. You have to prove it to the people you want to work for. (39:00)

My takeaway is that opportunities are not randomly bestowed upon people, they are by and large created by them. The way to create opportunities is to first and foremost, do interesting work. But no one can do everything, it’s highly unlikely that you’ll be a kick ass developer, an unicorn designer and a well rounded product manager at the same time. So do interesting work in an area / industry that you want to work in. Be great at that first.

Belief 1

There are numerous people saying this exact same thing— be “So Good that They Can’t Ignore You”. I’ve been noticing this idea continuously ever since I finished the book earlier this year. These podcasts are some examples of this. To get ahead in life, you must become great at what you do. To some extent the next example is also related to this idea.

Career Choices

On Startup School Radio epsiode 25, November 18th 2015, Elad Gil, an investor and entreprenuer spoke about his experience at Google, Twitter and starting his own companies and how that informed his view on career choices.

In your first role at a technology company, the most important thing you want to select for is first the market you’re in. Ask yourself: One. Is this a market that has a lot of future potential [to grow rapidly, to change the world as we know it]?
Two. The network of people at the company you want to be working at. The network may mean the people you’re working with day to day, it may mean the investors and advisors around the company, it may mean the founding team, but really it’s that group of people that can dramatically influence your trajectory. Famous example of that includes the PayPay network. If you were in there early, then you would’ve been exposed to LinkedIn, Facebook .. basicially every interesting company out there. If you joined the Google network early on, now people from Google are involved with running most of the major companies in Silicon Valley.
You see these really interesting alumni networks. If you join early, do a good job and get to know people that could have an enormous impact on your long-term trajectory. This is much more important than say the short-term compensation, the title or role.

The podcast host Aaron Harris from Y Combinator then raised the point that many people may find it easy or easier to evaluate salary when compared to quality of the network and the market opportunity, as people may find the latter two to be tremendously difficult or at least a lot trickier to evaluate.

Elad offered a different opinion.

On the network side, it’s actually not too hard to identify as long as you have some insider knowledge. That may be the hard part. There’s may be five venture firms that help to differentiate the companies in some sense, in terms of the likely brand of the company. When you talk with people, you can assess the calibre of the people you’re meeting with. You can see if everyone seem really good. I do think there are a few signs, but I agree, if you’re new to Silicon Valley, like I was at the time, it’s difficult. But once you’ve established yourself a little bit, or you’ve talked with people, that [understanding] can start to emerge.
When I talk about the market, I don’t mean the specific domain you’re working in, I mean the broader market of SaaS, consumer Internet, etc. Even if the one thing you work on fails, you’ll get to know people who are peer companies. You can move over to them. For example, When I left the telecom equipment industry, a bunch of people stayed in it, and those people’s career trajectory haven’t progressed as much as if they had switched into other areas that were having much higher growth. Growth ultimately creates opportunity.

Belief 2

The second belief is that no one can do a great thing alone — to do great things, people need to work in great teams and be in great markets. They need to leverage these two to reach higher. Of course, without being great at what they do first, they’d be able to leverage nothing.

So how do we find that high calibre team and the right market? Well, we do so by being in tune to the changes in world, observing and talking with people — so that we gain insider knowledge. But first, we ourselves, need to become highly skilled. It all starts there.

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